Patent GB-359164-A (GB)
IPC: C08K5/10
Filed: 1930-09-25
Abstract: Non-resinophoric esters of keto-aromatic acids are used as plasticizers.  The pseudomorphic esters of the keto acids may also be used.  The invention also includes the use of the reduced and/or hydrogenated keto acids, in which the keto group is reduced to a hydrocarbon.  The plasticizers may be used to plasticize natural or artificial resins, e.g. urea formaldehyde resins, casein plastics, polymerized resins, cellulose esters or ethers, or sulphur resins. They may be prepared by condensation of dibasic aromatic acids with an aromatic substance by the Friedel Crafts reaction.  There may also be present another plasticizer, e.g. sulphonamides or an ester of a dibasic acid such as an ester of phthalic anhydride.  As examples are the methyl, ethyl, propyl, butyl, amyl, cyclohexyl, tetrahydrofuryl, and benzyl benzoyl benzoates or substituted benzoyl benzoates. Esters of naphthoyl benzoic or the hydrogenated naphthoyl benzoic acids, and esters of acenaphthoyl benzoic acid and fluorene-carbonyl benzoic acid are included, as are the pseudomorphic esters, e.g. the pseudomorphic of methyl benzoyl benzoate, i.e. 3-methoxy-3-phenyl phthalide.  The esters are low-melting solids or viscous liquids. In examples in forming lacquers (1) phenol-formaldehyde is plasticized with butyl or mixed amyl benzoyl benzoates either alone or mixed with diethyl phthalate; (2) cellulose nitrate with butyl benzoyl benzoate; (3) cellulose acetate with butyl naphthoyl benzoate, and (4) a moulding composition, shellac, or other natural resins is plasticized with methyl benzoyl benzoate alone or mixed with methyl naphthoyl benzoate.  The Specification as open to inspection under Sect. 91 (3) (a) comprises also the use of keto esters derived from aliphatic dibasic acids, and an example in which urea formaldehyde is plasticized with methyl or butyl benzoyl acrylate.  This subject-matter does not appear in the Specification as accepted.ALSO:Esters of keto-aromatic acids, or their reduction products in which the keto group is reduced to a hydrocarbon radicle, or their tautomers, are used as plasticizers for natural or artificial resins, e.g. urea-formaldehyde resins, casein plastics, polymerized resins, cellulose esters or ethers, or sulphur resins. There may also be present another plasticizer, e.g. sulphonamides or an ester of a dibasic acid such as phthalic acid. As examples are the methyl, ethyl, propyl, butyl, amyl, cyclohexyl, tetrahydrofuryl and benzyl benzoyl-benzoates or substituted benzoyl-benzoates.  Esters of naphthoyl-benzoic or the hydrogenated naphthoyl-benzoic acids, and esters of acenaphthoyl-benzoic acid and fluorene-carbonyl benzoic acid are included, as are the tautomers, e.g. methoxy-phenyl-phthalide, which is a tautomer of methyl benzoyl-benzoate.  The esters are low melting solids or viscous liquids.  The acids corresponding to the specified esters may be prepared by condensation of dibasic aromatic acids with an aromatic hydrocarbon by the Friedel Crafts reaction.  In examples (1) glycerol-phthalate resin is plasticized with methyl benzoyl-benzoate; (2) phenol-formaldehyde with methyl naphthoyl-benzoate, methyl chlorbenzoyl-benzoate or methyl tetrahydronaphthoyl-benzoate; (3) phenol-formaldehyde with butyl or mixed amyl benzoyl-benzoates either alone or mixed with diethyl phthalate; (4) phenol-furfural with a mixture of methyl benzoyl-benzoate and butyl naphthoyl-benzoate or butyl benzoyl-benzoate; (5) polymerized styrol with butyl or mixed amyl benzoyl-benzoates; (6) polymerized itaconic acid with a mixture of methyl and butyl benzoyl-benzoate; (7) nitrocellulose with methyl benzoyl-benzoate alone or with phthalide; (8) cellulose nitrate with butyl benzoyl-benzoate; (9) cellulose acetate with butyl naphthoyl - benzoate; (10) polymerized cumeron and indene resin with methyl benzoyl-benzoate alone or mixed with dibutylphthalate; (11) glycerol-phthalate-Congo resin with a mixture of methyl benzoyl-benzoate and butyl naphthoyl-benzoate; (12) resin as in (11) and nitrocellulose with the plasticizer as in (11).  The Specification as open to inspection under Sect. 91 (3) (a) comprises also the use of keto esters derived from aliphatic dibasic acids and an example in which urea formaldehyde resin is plasticized with methyl or butyl benzoyl-acrylate.  This subject-matter does not appear in the Specification as accepted.ALSO:Non-resinophoric esters of keto-aromatic acids are used as plasticizers.  The pseudomorphic esters of the keto acids may also be used.  The invention also includes the use of the reduced and/or hydrogenated keto acids, in which the keto group is reduced to a hydrocarbon.  The plasticizers may be used to plasticize natural or artificial resins, e.g. urea-formaldehyde resins, casein plastics, polymerized resins, cellulose esters or ethers or sulphur resins.  They may be prepared by condensation of dibasic aromatic acids with an aromatic substance by the Friedel Craft's reaction.  There may also be present another plasticizer, e.g. sulphonamides or an ester of a dibasic acid such as an ester of phthalic anhydride.  As examples are the methyl, ethyl, propyl, butyl, amyl, cyclohexyl, tetrahydrofuryl and benzyl benzoyl benzoates or substituted benzoyl benzoates.  Esters of naphthoyl benzoic or the hydrogenated naphthoyl benzoic acids, and esters of acenaphthoyl benzoic acid and fluorene-carbonyl benzoic acid are included, as are the pseudomorphic esters, e.g. the pseudomorphic of methyl benzoyl benzoate, i.e. 3-methoxy-3-phenyl phthalide. The esters are low melting solids or viscous liquids.  In examples which include lacquers and moulding compositions (1) glycerol-phthalate is plasticized with methyl benzoyl benzoate; (2) phenol-formaldehyde with methyl naphthoyl benzoate, methyl chlorbenzoyl benzoate or methyl tetrahydronaphthoyl benzoate; (3) phenol-formaldehyde with butyl or mixed amyl benzoyl benzoates either alone or mixed with diethyl phthalate in forming a lacquer; (4) phenol-furfural with a mixture of methyl benzoyl benzoate and butyl naphthoyl benzoate or butyl benzoyl benzoate; (5) polymerized styrol with butyl or mixed amyl benzoyl benzoates; (6) polymerized itaconic acid with a mixture of methyl and butyl benzoyl benzoate; (7) nitrocellulose with methyl benzoyl benzoate alone or with phthalide; (8) cellulose nitrate with butyl benzoyl benzoate; (9) cellulose acetate with butyl naphthoyl benzoate; (10) shellac or other natural resins with methyl benzoyl benzoate alone or mixed with methyl naphthoyl benzoate; (11) polymerized cumeron and indene resin with methyl benzoyl benzoate alone or mixed with dibutylphthalate; (12) glycerolphthalate-congo resin with a mixture of methyl benzoyl benzoate and butyl naphthoyl benzoate; (13) resin as in (12) and nitrocellulose with the plasticizer as in (12).  The Specification as open to inspection under Sect. 91 (3) (a) comprises also the use of keto esters derived from aliphatic dibasic acids and an example in which urea formaldehyde is plasticized with methyl or butyl benzoyl acrylate. This subject-matter does not appear in the Specification as accepted.